Men get very few chances to add a bit of flair to their dressing – they can pop a playful sock (see Justin Trudeau), have a cool cuff to turn up (thank you, Paul Smith) and go for a statement watch. Frills and furbelows are mostly female territory – so what can men do when they want to take their style to the next level? Headwear is the answer.

A once ubiquitous item, hats fell out of favour with the rise of the automobile – the roof was too low under which to wear a hat, plus, you were already sheltered from the elements. The Second World War also had an effect: Men said they didn’t like to be reminded of wearing helmets. John F. Kennedy is also said to have given hats their final death knell. Known for his youthful and stylish image, he wanted to project that he was modern and approachable by going about his official business bareheaded.

Now, hats are a choice versus a necessity and an easy way for men to up the style ante. For a masterclass in selecting and wearing chapeaux, we turned to Karyn Ruiz, of Toronto’s Lilliput Hats, who collaborated with the late great singer, The Tragically Hip’s Gord Downie on headgear for his final Man Machine Poet tour. Ruiz cites Downie as a huge influence on Canada’s hat-buying scene, with men coming in and requesting the “Downie hat” (she makes a tribute version).

Ruiz has some helpful tips for navigating which hat to wear, when and how. “The panama is a classic starter hat. Especially for spring, summer and early fall,” says Ruiz. “Right now, I am recommending a white or alabaster/bone panama with a black or baby blue band.”

She has a few key considerations when trying one on: “Make sure the crown isn’t too high, and the brim is the right width. I recommend a three-inch flat brim.” Ruiz points out that your height and head size should come into play. “With a really big guy, it can just seem like it’s perched there, so then a slightly wider brim can help balance the look.”

Anthony Hopkins is a keen panama wearer, both on and off the screen, famously sporting one as the psychopathic but soigné Hannibal Lecter. Benedict Cumberbatch dons his as part of his red carpet ensembles – most notably his elegant Gatsby-esque white suit and white Lock & Co. Hatters panama for the Met Gala in 2019 – and out at British summer events like Wimbledon and the Chelsea Flower Show. Sean Connery was fond of his Montecristi pulled low down over his famous eyebrows.

“The demand for panamas is off the charts,” says Ruiz. “I get my straw from Ecuador – it’s a bespoke woven process done by families for centuries – they can’t keep up with production. I now order in December so that I can have it in time for spring.” Despite its name, the panama hat originates from Ecuador where they are handwoven from the fibres of the toquilla palm tree.

Our summer season in Canada is notoriously short, so investing in a bespoke panama may not be feasible. Ruiz says there is no shame in wearing felt, even during the warmer months. “If it’s a natural fibre it breathes, and if people really want to make an investment, we encourage them to wear their felt into the summer. As the sun goes down and you’re having dinner on a patio, it’s more than acceptable. We’re practical people and if you’re going to spend the money and buy one hat, I’d suggest a mid-tone or light colour so that it works year round.”

Fedoras typically have an indented crown, around ten to 15 centimetres high, with a soft brim from five to 10 centimetres wide, but from there a delightful number of iterations can happen. The crown can have a centre dent, teardrop or diamond shape. Guitarist John Mayer loves a wider brim and boho, decorative hat band; and hockey star and NHL analyst, P.K. Subban, a newcomer on the hat scene, goes for bold jewel tones with lush silk bands and eye-catching brims. “He is really upping the game, style-wise,” says Ruiz. Perhaps the most famous film fedora belongs to Harrison Ford’s character, Indiana Jones. It was made by Herbert Johnson Hatters in London, U.K., and the original is in the Smithsonian Collection.

For those who aren’t comfortable in a structured hat, the flat cap and the bucket hat can fill in the style gap. Cillian Murphy’s character in Peaky Blinders is credited for bringing the flat cap back to men’s wardrobes. “We find a lot of guys like the more relaxed, retro look of a flat cap. Made out of a nice Harris tweed, they can top off an outfit beautifully,” says Ruiz. Even though flat caps are more casual than panamas and fedoras it’s still essential to get the fit right. Like a baseball cap, it should be gently snug around the sweatband without being too tight, with extra room in the crown so the fabric doesn’t have to stretch over your head. Opt for a classic material like wool, tweed or cotton for breathability and form. Flat caps can transition from day to night, with devotees such as Idris Elba using them to top off a stylish suit.

Bucket hats used to be something that were seen at the beach or the lake, picture Henry Fonda as Norman Thayer Jr. wearing his as he potters about his cabin in On Golden Pond. Then, in the early 2000s, hip-hop brought them from the country to the city, as rappers and their fans adopted the Kangol brand, embracing their distinctive bucket hats as urban streetwear. Recently, with the rise of the Dadcore fashion movement, they’ve experienced a resurgence. Brad Pitt is a bucket hat diehard, he’s been spotted topping his outfits with a white bucket hat by SSAM, an Italian luxury brand, and his latest is a fuzzy shearling one from Hunter (now sold out, of course).

While we’re on the subject of caps, we can’t avoid the omnipresent baseball cap. Ruiz points out that if you are going to wear one off the field, the best way to elevate the look is to choose one without a logo, in the manner of the ultimate quiet luxury pinup, Succession’s Kendall Roy, in his Loro Piana cashmere cap, and to never, ever, wear it backwards (let alone with sunglasses on the back).

The same rules of civility apply for baseball caps as with more formal hats: Take it off in a restaurant, in someone’s home, at the table, in a house of worship, indoors at work, in public buildings and at a movie or any indoor performance. And nothing is more stylish than good manners, so if you’re out and about and wearing a hat, don’t forget to tip it upon meeting someone.

— Antonia Wyatt